(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester → (S)-N-[3-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]-sulfonyl]tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

HRID 2351087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2351087
[OH:1][C:2]1[C:3](=[O:40])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:17]([NH:20][C:21]([N:23]3[CH2:26][C@H:25]([NH:27]C(=O)OCC4C=CC=CC=4)[C:24]3=[O:38])=[O:22])(=[O:19])=[O:18])[C:12]2=[O:39])=[O:9])[NH:6][CH:7]=1>CN(C)C=O.[Pd]>[NH2:27][C@H:25]1[CH2:26][N:23]([C:21]([NH:20][S:17]([N:13]2[CH2:14][CH2:15][CH2:16][N:11]([NH:10][C:8]([C:5]3[NH:6][CH:7]=[C:2]([OH:1])[C:3](=[O:40])[CH:4]=3)=[O:9])[C:12]2=[O:39])(=[O:18])=[O:19])=[O:22])[C:24]1=[O:38]

Komponenten

4

Edukt 1

HCID 86743424(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Produkt 1

HCID 53731386(S)-N-[3-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]-sulfonyl]tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4.95 g (8.57 mmol) (S)-[1-[[[[3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was dissolved in 50 ml N,N-dimethylformamide. After the addition of 2.5 g palladium on carbon, the mixture was hydrogenated for 1 hour. The catalyst was removed and subsequently the filtrate added dropwise to 500 ml isopropanol. The desired product was filtered off, slurried with either and dried in vacuo. Yield 3.03 g, melting range 160°-220° C. (dec.).

Aufarbeitung

  1. customThe catalyst was removed
  2. additionsubsequently the filtrate added dropwise to 500 ml isopropanol
  3. filtrationThe desired product was filtered off
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1506582b737344328de7790582027360
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04871841

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